10 Greatest Philip Seymour Hoffman Performances

On the 2nd of February, 2014, actor Philip Seymour Hoffman was found dead in his Manhattan apartment from a combined drug overdose. The news was unexpected for several reasons; Hoffman was only 46 years old, which is far too young for anyone to pass away, regardless of their profession. It was also unexpected because of how prominent he was as a contemporary actor. He had recently appeared as Plutarch Heavensbee in The Hunger Games: Catching Fire, and even more recently at Cannes to promote two films he appeared in; the first is Anton Corbijn’s A Most Wanted Man, the eagerly-awaited adaptation of the John Le Carre novel of the same name, where Hoffman acts opposite heavyweights Robin Wright and Willem Dafoe as a German detective. The other is God’s Pocket, the directorial debut of Mad Men actor John Slattery, where Hoffman plays a thief. To see him appear in these films will, like James Gandolfini’s equally untimely death, bring an undercurrent of melancholy to the proceedings. He was even mid-way through shooting the final instalment of The Hunger Games trilogy – whether he’ll appear in Mockingjay Parts 1 & 2 is unknown, although rumours have been circulating that he will be digitally recreated in the remaining scenes he had left to shoot.

Yet the ultimate reason why Philip Seymour Hoffman’s death was so shocking was because of how well-respected and loved he was, not just as an actor but as a person. Admittedly, I never met him, but I spoke to someone recently who had worked with him for a time. She described him as a difficult man, typically professional but, at times, unpleasant to be around – as many struggling addicts often are. However, she told me how all that changed when he stepped in front of a camera. Gone was the Hoffman she knew, instead appeared a man of gravitas and vulnerability. He garnered a considerably warmer reputation with the actors he worked with, indicated by the hundreds of tributes which flooded in following his death, from collaborators and friends such as Robert De Niro, Julianne Moore, George Clooney, Cameron Crowe and more. One of the most moving and public of these was Cate Blanchett, finishing her exceptional BAFTA acceptance speech by dedicating the award to the late actor.

It was clear that both critics and friends appreciated the wonderful qualities Hoffman had on-screen. He was most commonly known for his ability to make even the smallest supporting roles in his films memorable, evident even in his early appearance as a conceited schoolboy in Al Pacino vehicle Scent of a Woman, and evident in both the most humble art house film to the noisiest big-budget blockbuster. Out of all the critics, David Fear of Rolling Stone was one of the few to perfectly capture what made the actor so special:

He was a transformative performer who worked from the inside out, blessed with an emotional transparency that could be overwhelming, invigorating, compelling, devastating.

It’s very true, and it’s this vulnerable, versatile quality that forms the backbone of this list I created, to distinguish between the good, the great and the outstanding performances of Hoffman’s career. A few films didn’t quite make the cut; I would have liked to have included Doubt, where he comfortably outshone a cast all turning in incredible performances. Think of that as #11. Elsewhere there are several films where he took on less significant roles but still brought a touch of class to the proceedings, as is the case with Moneyball and The Ides of March; both very good films, but Hoffman’s presence in these films isn’t quite significant enough for me to put them on my list. If I’d included voice performances then Mary and Max would have made the cut, although in order to make this manageable I had to impose some restrictions. His villainous turn was easily the best thing about Mission: Impossible III, and I even liked him in Twister chanting “FOOD!” at Helen Hunt. Oh, and if I hadn’t had so many problems with the film itself I would have included Before the Devil Knows You’re Dead, where he shared excellent chemistry with his co-star Ethan Hawke. But enough of that – the following are what I believe to be the best performances the late actor had to offer.

10. 25th Hour (2002)

As I hope this list will prove, Philip Seymour Hoffman was an expert at making us sympathise with deeply flawed characters who make terrible decisions, and introverted high school teacher Jacob Elinsky is no exception. One of my favourite Spike Lee joints – actually, one of my favourite films, period – it’s far more contemplative than Lee’s other work since it’s a measured, melancholic examination of post-9/11 America. It’s a smart film, perhaps a great film, and key to this is the performances, particularly Barry Pepper and, of course, Philip Seymour Hoffman. The scene which encapsulates what makes his role so memorable is one of the most painfully awkward scenes Hoffman ever starred in (quite a feat considering that bit with the handjob in The Master). As the three friends prepare to enter a nightclub, Jacob (Hoffman) invites a student he has a crush on (Anna Paquin) to join them. He knows he’s already on shaky moral ground but decides, after a few drinks, to kiss her. Bad move. Following an achingly long shot of the kiss, both leave to go their separate ways, with neither remotely happy about what just happened. Hoffman’s expression afterwards in a classic Spike Lee “glide” shot is unforgettable.

9. Almost Famous (2000)

In Cameron Crowe’s sweet semi-autobiographical 70s drama, it’s easy to forget the small appearance Philip Seymour Hoffman makes as music critic Lester Bangs. There was a lot else going on, like bad hair, teenage angst, and a great period soundtrack; easily one of the most naturally likeable films of the noughties. But then again, how could you forget Lester Bangs? In the five minutes or so of screen time he has in Almost Famous he comes out with the most straightforwardly honest and helpful advice imaginable to anyone, let alone an impressionable young protagonist like William Miller. Just listen to his speech on being “uncool”, one of Hoffman’s best moments as an actor. Isn’t that something any awkward teenager wants – needs – to hear? I only wish I could travel back in time and show this scene to myself at fifteen. Cameron Crowe based this film off his own experiences profiling The Allman Brothers Band. Whether or not he had such a figure in his life I’m not sure, but Hoffman imbues this character with such likeability that he makes you wish you had a mentor like Lester Bangs growing up.

8. Boogie Nights (1997)

After an amusing cameo in Hard Eight, Hoffman re-teamed (and eventually developed a lifelong friendship) with Paul Thomas Anderson, to take on a small role in his incredible epic charting the rise and fall (and rise again) of the porn industry. His Scotty J. doesn’t appear until some way into the film, but when he does it’s quite a sight. We hear the sound of Hot Chocolate’s “You Sexy Thing” as he awkwardly shambles into view, with both the image of his unattractively plump belly poking out of his vest and his slurred, nervous speech pattern being the most memorable aspects of this performance. Obviously Scotty J. is gay in a society where it’s not seen as acceptable to be gay, and this manifests itself poignantly in a scene in front of Scotty’s new car – a car he bought solely to impress the well-endowed Dirk Diggler (Mark Wahlberg), whom he tries to kiss, only to be violently rejected. Hoffman really seemed to have a thing for painful romantic encounters, and each time I watch the scene there’s a part of me which dies a little when he begins to berate himself for his stupidity. Such an emotionally needy performance is no easy feat whatsoever.

7. Happiness (1998)

Continuing the running theme of sad, lonely characters, Allen in Happiness might be one of the saddest, loneliest character I’ve ever seen in a film, or at the very least Hoffman’s most downwardly depressing and unflattering performance. He plays someone who makes obscene phone calls to women, with one particularly memorable scene having him sitting in his underwear masturbating while talking down the phone – a scene Hoffman recalled as particularly difficult:

It’s hard to sit in your boxers and jerk off in front of people for three hours. I was pretty heavy, and I was afraid that people would laugh at me. Todd said they might laugh, but they won’t laugh at you. He saw what we were working for, which was the pathos of the moment.

It’s nothing short of remarkable that the actor found the courage to put aside personal embarrassment in favour of the artistic integrity of the picture (can you imagine someone like Tom Cruise doing something similar? No, Vanilla Sky does not count) and ranks as one of the best, most shameless degradations of self-image in film history. In lesser hands Allen could have come across as aggressively perverted and creepy (which are undeniable elements of his pasty character) but instead comes across as sad and inspiring pity rather than disgust – “pathos” really is the key word here.

6. The Talented Mr Ripley (1999)

A world away from Allen in Happiness, this is a role which really showcases Hoffman’s range as an actor. He comes on screen in this swaggering explosion of life, dancing out of his red sports car and uttering one of his greatest lines; “God, don’t you want to fuck every woman you see at least once?” He absolutely captures the role of the friend-of-a-friend you can’t stand, and watching his Freddie Miles get under the skin of Matt Damon’s Tom Ripley is delightful. Who can forget that scene where Freddie probes a jealous Tom on the boat as he watches Jude Law have sex? “Tommy. How’s the peeping? Tommy, how’s the peeping? Tommy. Tommy. Tommy. Tommy. Tommy.” It’s Hoffman at his most unlikeable and obnoxiously confident, as representative of the bully who picked on us in school as he is of privileged upper-class values. We feel little sympathy when he finally has his head bashed in by the same stone bust he was so carelessly resting his hand on moments before, although that’s not to say we’re on Ripley’s side; having him imitate a conversation with a corpse he’s trying desperately to conceal is a unforgettably disturbing image.

5. Charlie Wilson’s War (2007)

Maybe the only thing better than a Philip Seymour Hoffman performance is a Philip Seymour Hoffman performance written by Aaron Sorkin. This is easily the actor at his most entertaining, playing a gruff CIA agent who brings this thinly-veined layer of anger to every scene he’s in. You feel like he could explode at any time, and sometimes he does. In the days immediately after Hoffman’s death this clip circulated of the scene where we first meet his character. It’s a classic, funny scene – perhaps the best in the film – and what makes it so great is the way Hoffman plays with our expectations. Our initial impression of his character is that he’s a rude, arrogant man refusing to apologise. We then begin to understand the frustration he feels at the system, and how his character’s important work for the agency goes unnoticed. Finally, as he asks “How was I?” we realise it was all a trick, a theatrical performance for the benefit of his co-workers, and, ultimately, us. There’s also the smashing of the window, one of those wonderful Sorkin moments where we get a hilarious pay-off to something introduced at the start of the scene – like the ceiling in Josh’s office collapsing in The West Wing – and Hoffman carries it off with such verve that you feel like getting up and applauding. Alongside being the best thing about Along Came Polly, Charlie Wilson’s War proved that Hoffman can be very funny indeed, and where the film occasionally struggled to maintain the balance between comedy and drama Hoffman effortlessly succeeded.

4. Capote (2005)

This was the film that won Philip Seymour Hoffman the best actor Oscar, and for a good reason. His transformation into Truman Capote was astonishing, the complete immersion into the role enough to make Daniel Day-Lewis blush. Most people talk about the striking voice Hoffman does (understandably so, considering the typically gravelly, laconic voice is a trademark of the actor), but there’s so much more going on here. It’s the little things that count – the way he sits, legs crossed, cocktail delicately perched in hand, effortlessly spinning an entertaining anecdote at a party – that you believe he simply is Capote. It’s a flawed film otherwise, sketching over some important characterisation of the supporting cast, but Hoffman compensated where the script lacked. His Capote is self-absorbed, irritable, often childish but assuredly human, and Capote is all the more tragic because of this performance – of a man who became one of the greatest authors in America, but at the cost of his soul.

3. The Master (2012)

I’ve brushed over Philip Seymour Hoffman’s involvement with Paul Thomas Anderson so far but I think it can be safely said that, out of all his collaborators, Anderson really understood the actor best. Appearing in 5 out of 6 of his films, Hoffman was frequently cast in his most challenging roles – see spots #8 and #2 in this list – but his appearance as the deuteragonist of The Master was the first time he had been cast in a prominent leading role by the director.

And what a role. In this difficult but rewarding film, Hoffman plays the charismatic leader of cult “The Cause”, which may or may not be based on Scientology (it’s certainly worth noting that the actor resembles founder L. Ron Hubbard quite a bit). That’s not really important, though – what is important is how Hoffman plays this man, who captures the hearts and minds of his devoted followers, with real complexity. When we first see Lancaster Dodd in public he’s giving an almost playful performance, and initial impressions of charlatanism are dispelled as we see a man who genuinely cares for his flock. Yet as the film progresses we see the cracks in this façade begin to emerge, such as the scene where he angrily denounces an opponent of his work as a “pig-fuck”, or the moment where loses him temper at devotee Laura Dern for questioning the choice of words in his latest book.

He acts opposite Joaquin Phoenix who gives the more animalistic, louder performance – some might even say more impressive. But there’s an impressive contrast between the two performances, where the duo essentially play opposites but are inexplicably drawn to one another. And while Phoenix’s visible incarnation of rage and confusion is disturbing, Hoffman’s spare moments of anger are infinitely more terrifying, and his moments of vulnerability more moving; who could forget his astonishingly vulnerable and deliberate rendition of ‘Slow Boat to China’?

2. Magnolia (1999)

It was between this and The Master for the #2 spot on my list. Both are fine Paul Thomas Anderson films, but, more importantly, both contain fine Philip Seymour Hoffman performances. “But wait,” I hear you cry, “isn’t Hoffman only one part of a larger ensemble in Magnolia? He doesn’t even have the best part! Why would you choose this over his more prominent role in The Master?” Well, all this is true. Hoffman has a relatively small role in Magnolia, that of the dying Jason Robard’s private nurse, who, as part of his final wish, reaches out to his sex-guru son, played by Tom Cruise. And yes, both of these actors (and other participants in this film such as Melora Walters, John C. Reilly and Philip Baker Hall, all of whom are wonderful) seemingly have meatier, more dramatic roles – indeed, one of my favourite scenes is where Tom Cruise finally confronts his cancer-ridden father, a scene which may have single handedly won the man a Golden Globe.

But Philip Seymour Hoffman does something more important here, and accomplishes a task which lesser men would have baulked at. In a film filled with complicated, difficult characters, the character of Phil Parma is arguably the most sympathetic. He’s a simple nurse, whose job is to care for a dying old man. He’s bumbling, awkward – there’s a hilarious scene where he orders porn magazines over the phone – but, most importantly, he’s honest. Every scene, Hoffman wears his heart on his sleeve and never takes it off. And isn’t that the most terrifying thing for an actor to do? To expose yourself to the world as a human being, when you spend most of your time hiding your true self? His emotional and selfless performance still blows me away to this day, even when there’s so much else going on in Magnolia to love (watch this scene if you don’t believe me). Sometimes the best acting is knowing when to step aside.

1. Synecdoche, New York (2008)

There was no doubt surrounding what my top choice would be for this list. Out of all the astonishing roles Philip Seymour Hoffman had as an actor, out of all the swaggering best friends, quiet men of authority, enigmatic artists and troubled anti-heroes, none were quite so powerful and affecting as his theatre director Caden Cotard. In an ambitious, depressing, profound and rather confusing film about… well, everything, Synecdoche, New York was rooted in Hoffman’s incredible central performance. The film opens with a sad scene between Caden and his wife (Catherine Keener, reunited again after Capote) who, it seems, no longer loves him. It doesn’t get much better from there. Phil’s character is pathetic and frustrating, whose flaws are nothing short of infuriating (he cries and apologises before sex, he’s a hypochondriac obsessed with how he’s going to die). Yet he gives this character such humanity and vulnerability and sadness – more so than any sad character he’s ever played – that you can’t help but care deeply for him.

One of the most painful scenes of the film is where he is told “Everyone is disappointing the more you know them.” His reaction is heartbreaking, and this kind of tragic moment is repeated about fifty times throughout the film, making for an emotionally draining experience. But this is not a hopeless film, or at least it shouldn’t be; it’s supposed to be about us, and Hoffman’s performance encapsulated that. He played the perfect everyman, who commands us to sympathise with a character at their darkest or most unlikeable, and what makes the role so affecting is that we can understand him almost too well – a talent Hoffman had throughout his career, having us empathise with heroin addicts to paedophiles, but a talent which truly reaches its peak here.

I came away from this film feeling confused and depressed. I knew that I’d seen something good, maybe something great, but I was unable to place what, exactly, that was. Yet in a mess of ambiguities and convolutions there was one thing I was sure of – that Philip Seymour Hoffman had just given the performance of a lifetime. It’s hard to imagine, but, given time, perhaps he could have bested his Caden Cotard. As it is, this is more than we deserved. He will be deeply missed.

47 Comments

Great list (as well as great ordering of the list, I definitely agree with each of Hoffman’s film placements). Such a sad thing to see a talent like him go so early, we’re super fortunate that he gave us so many excellent performances! He certainly won’t be forgotten. Good work!

I saw him as Willy Loman in Arthur Miller’s Death of a Salesman on Broadway. It was the greatest show I’ve ever seen, his performance making it so. It was amazing seeing him perform live and it is a shame no one will be able to anymore. His intensity was amazing and he truly fulfilled the characters he played. He will be missed.

I imagine the hard part about writing this article is just picking ten. He not only made good movies great, but bad movies watchable, such as with “Patch Adams” or “Twister.” He left too soon, but he did leave a filmography of must-watches.

Anyway, Hoffman’s talent is unprecedented, definitely. In Happiness and Boogie Nights, he plays such a gross disgusting man (well, Boogie Nights, not gross, but certainly sad and tough to deal with), and it takes a lot of talent and goodness to want to play a role like that and shine with it. Such a great man, actor.

Absolutely loved the article; I was crushed when I found out he had passed away–I had seen him play so many heart-wrenching characters (Synecdoche being the most impressive) and I just couldn’t believe that no one will ever be able to see all the different kinds of films he could have done. He was truly an incredibly gifted actor

Philip Seymour Hoffman is a study in quirky character roles that bring power to a film. One of my faves he will be missed. His personal affectations were unusual and on display in each character he portrayed. He was a man of mystery–always holding something back it seemed. And indeed I guess he was. Heroin is a powerful killer.

The fact that the man had to hide his habit from others says a lot about how gullible most of society can be when it comes to those who seek to numb their wounds and despair by the use of mind-altering substances.

Unfortunately for PSH, the substance in question was not one which is somehow exempt from media sensationalism, political propaganda, and cultural taboos – such as ethanol (alcohol), which has been repeatedly shown to be neurotoxic (brain damage), hepatotoxic (liver damage), and cardiotoxic (heart damage).

Rather, it was diacetylmorphine, known as Heroin, because it was once sold as Heroin in pharmacies all over the US by the makers of Aspirin (Bayer).

I’m sorry that society did not approve of your method of trying to drown your sorrows Philip. I am confident that one day, when enough of the elites have suffered the same fate, things will drastically change for the betterment of every American.

As we are living in the so-called “information age” I’m confident that many Americans will soon do their own research on this controversial topic, and discover some fascinating statistics, such as the fact that each year, more Americans die from second-hand smoking than all street drug deaths in the US combined. Or, perhaps they’ll find that Methamphetamine is actually a prescription drug in the US, and that Heroin is still prescribed in several first-world countries.

I don’t care what substance you abuse, it is still idiotic. Self control, and personal responsibility are both important things in this world. So have some self control, and live your life in moderation. If you don’t, don’t expect the entire world to feel bad for you, it is your fault. Of course it is sad for his family and friends that he killed himself, for the rest of us there will be another actor to take the rolls. If all these celebrity deaths prove anything, it is that money does not buy happiness.

While these are certainly some of his “best” movies, I do love his performance in “Along Came Polly,” solely because he took a bad movie and stole every scene he was in. That’s quite an accomplishment.

I loved him in Big Lebowski, I still find his awkward laughter in that film hilarious. Does anyone remember when Michael Caine said that the sequel to The Dark Knight would have Hoffman in it as The Penguin? That would have been pretty bad ass.

It’s rare that I actually agree with these “best of…” film lists to the extent that I agree with this one. Then again, it would be hard to compile a list of this dude’s films that was anything other than excellent.

Great list. Hollywood just got slightly lamer for his loss. A terrific actor.

While these are all good choices, one of my personal favorite Hoffman performances still remains his role in ‘Doubt.’ Hoffman opposite Meryl Streep on screen is nothing short of phenomenal and deeply emotional. Those two are absolutely fantastic on their own, but together they bring out the absolute best in each other, so imagine the extremely high caliber of performance level occurring. In that film, they provided a master class in acting, and Hoffman was a massive part of what made that film so breathtaking. His absence from cinema will definitely be felt and missed.

This is a great list, Sam! I really like the way you described his performance in “Charlie Wilson’s War”, which I thought was incredible. I wonder what you might think about Philip Seymour Hoffman’s performance in 2007’s “Before the Devil Knows You’re Dead”-a dark, convoluted heist/family psychodrama with Ethan Hawke, where PSH’s character, ironically, is battling an addiction with heroin?

Fabulous list and I’m so glad you mentioned Mary and Max. More often than not, lists like this overlook the body of an actor’s work and only focus on their own favorites. Hoffman has been amazing in every film he has appeared in, so I do not envy your project of choosing the top 10 best. Great work though, and great descriptions of Hoffman in each.

Hoffman’s performance in The Master in particular stands out to me- a charismatic master manipulator. When we discover both slight and large cracks in his folksy demeanor (him screaming at the skeptic comes to mind), we are remarkably shocked, considering how most of us have realized that he’s based on L. Ron Hubbard. A testament to Hoffman’s skills as a chameleon.

Whether or not I agree with the order is another conversation. I enjoyed Hoffman’s performance in “Boogie Nights” and “Charlie Wilson’s War”. I plan to watch the others mentioned in your article. Hoffman had a way of making you believe he was the character he was representing. His ability to make each character fit like a glove will always be revered by the community. We have lost a great one.

This is a great list of movies, and Magnolia is one of my all-time favorites, but I really enjoyed him in Love, Liza. That movie was about him being an addict (he’s addicted to huffing gasoline) and he played the part well.

I would probably include Flawless on my own list, because both Hoffman and De Niro are phenomenal. Although I would say Hoffman was almost always phenomenal; I have never been so affected by a celebrity’s death as his, because his talent was just incredible. It’s such a waste.

I’m not saying this sarcastically, I ADORED him in Along Came Polly. Really solidified Philip Seymour Hoffman as an actor who could do anything on screen he wanted, whenever he wanted. Also was fantastic in Doubt- wasn’t a fan of the book, loved the movie because of his performance. RIP

I remember the first time this dude jumped on my radar, it was because Final Fantasy X and the villain Maester Seymour. Philip Seymour Hoffman was the first time I ever seen the name Seymour after Final Fantasy X and I remember thinking how cool it was that he had the same name as the villain in my favorite game!! Ha, nostalgia is so cray!